by Mark

Gender: Male
Age: 38
Race/ethnicity: White
Current location: Chicago
Highest education received: Not graduated from high-school
Occupation: Security firm
Relationship status: Married
Religious affiliation: NA
How religious are you? A little
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Swinger
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0


How long ago did this hookup happen? 2 month

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Curious Fling

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Short black man with a massive member

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was on location at a site i manage discussing an incident with one of the security managers that works for me at the firm, and i could not stop staring at the bulge in his pants it made me feel very awkward.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We had some casual conversation and he noticed me starring and asked if i wanted to see it before i could answer he pulled it out of his pant and immediately made my penis more erect than it had been in years. he saw that and we had not reason to discuss anything any further i proceeded to do something i never thought i would do i dropped down and started to have oral sex with him, he came in my face on on my beard which was a bit awkward he then proceed to pull me up and slip finger in my pants and into my anus, i like it and it mad me orgasm he asked if i water more i said yes and that is when he pulled my pants down bent me over and slid his big penis indie me at first in burned then but after about 2 minutes it felt so good i could not help but cum again.

Did you have an orgasm? Did your partner(s)? Yes i orgasmed multiple times and so did he.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No precautions were taken he was inside me bare as it was my first time with another man.

What were your REASONS for having this hookup? I don’t know, curiosity i guess.

Were alcohol or drugs involved? If so, how much? No

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt a bit ashamed and awkward as i am his manager and i had never been with another man before.

To whom did you talk about the hookup? How did they react? I spoke with my wife and she was understanding, we are swingers and she has been with men in front of me she suggested that i invite him over so she could have sex with him in front of me i like that idea.

Was this a consensual and/or wanted experience for you? For your partner? Yes i think so.

Do you regret this hookup? If so, why? Yes and no.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It really opened my eyes to being with other men.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Not at all negative

You have a hookup story to share? Submit it here!

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!